Biomimetic Total Synthesis of (−)-Neroplofurol and (+)-Ekeberin D4 Triggered by Hydrolysis of Terminal Epoxides

  • Takeshi Kodama
    Department of Chemistry, Graduate School of Science, Osaka City University
  • Shingo Aoki
    Department of Chemistry, Graduate School of Science, Osaka City University
  • Tomoki Matsuo
    Department of Chemistry, Graduate School of Science, Osaka City University
  • Yoshimitsu Tachi
    Department of Chemistry, Graduate School of Science, Osaka City University
  • Keisuke Nishikawa
    Department of Chemistry, Graduate School of Science, Osaka City University
  • Yoshiki Morimoto
    Department of Chemistry, Graduate School of Science, Osaka City University

抄録

<jats:title>Abstract</jats:title> <jats:p>To accumulate the chemical basis of epoxide-opening cascade biogenesis, chemical syntheses of sesqui- and triterpenoids were performed. The biomimetic total syntheses of (−)-neroplofurol (1) and (+)-ekeberin D4 (2) were accomplished by protic acid-catalyzed hydrolysis of the terminal epoxide from nerolidol diepoxide 3 and squalene tetraepoxide 4 through single and double 5-exo cyclizations in intermediates 5 and 6, respectively. This chemical reaction mimics the direct hydrolysis mechanism of epoxide hydrolases, enzymes that catalyze an epoxide-opening reaction to finally produce vicinal diols.</jats:p>

収録刊行物

  • Chemistry Letters

    Chemistry Letters 43 (10), 1662-1664, 2014-10

    Oxford University Press (OUP)

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